2-(acylimino)thiazolidine herbicides

ABSTRACT

Herbicidal compounds have the formula &lt;CHEM&gt; in which W is sulfur; X is hydrogen, halogen, nitro, cyano, perhalomethyl, difluoromethyl, pentafluoroethyl, C1-C4 alkyl, C1-C4 alkoxy, trifluoromethylthio, difluoromethoxy, trifluoromethoxy, tetrafluoroethoxy, methylsulfonyl, trifluoromethylsulfonyl, phenoxy, pyridyloxy, halo-substituted-phenoxy or -pyridyloxy, trifluoromethyl-substituted-phenoxy or -pyridyl oxy, C1-C4 alkyloximinomethyl, benzyloximinomethyl, 1-(C1-C4 alkyl)-oximinoethyl and 1-benzyloximinoethyl; Y is hydrogen, halogen, nitro, cyano, perhalomethyl, difluoromethyl, pentafluoroethyl, C1-C4 alkyl, C1-C4 alkoxy, trifluoromethylthio, trifluoromethoxy, tetrafluoroethoxy, methylsulfonyl and trifluoromethylsulfonyl; Z is hydrogen or fluoro if Y is hydrogen, or hydrogen if Y is other than hydrogen; R1 is hydrogen, methyl, ethyl or chloromethyl;  A is oxygen, sulfur, -NH-, -C2H4- or &lt;CHEM&gt; in which R3 and R4 are independently hydrogen, methyl or methoxy; and R2 is alkyl; carboalkoxy; carboalkoxyalkylene; haloalkyl; alkoxy; optionally methylsubstituted cycloalkyl; phenyl; substituted phenyl; phenoxy; halophenoxy; styryl; p-chlorophenylsulfonyl; haloalkylcarbonyl; naphthyl; halonaphthyl; benzoyl; halo-substituted benzyl; polycyclic aliphatic; mono- or dialkylamino, benzoyl; or a 5- to 6-member heterocyclic ring containing 1-2 oxygen or sulfur atoms, optionally substituted; and m is 0 or 1.

BACKGROUND OF THE INVENTION

The present invention relates to certain 2-(acylimino)thiazolidine herbicidal compounds, compositions, and methods of use.

There are a number of different types pof herbicides presently sold commercially, and these fall into two general categories. The categories are pre-emergence and post-emergence herbicides. The pre-emergence herbicides are normally incorporated into or applied to the soil prior to the emergence of the weed plants from the soil, and the post-emergence herbicides are normally applied to plant surfaces after emergence of the weeds or other unwanted plants from the soil. Some herbicides are effective both as pre- and post-emergence herbicides. The iminothiazolidines of this invention fall into that category.

DESCRIPTION OF THE INVENTION

The compounds of this invention have the formula: ##STR3## in which W is oxygen or sulfur;

X is hydrogen, halogen, nitro, cyano, perhalomethyl, difluoromethyl, pentafluoroethyl, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, trifluoromethylthio, difluoromethoxy, trifluoromethoxy, tetrafluoroethoxy, methylsulfonyl, trifluoromethylsulfonyl, phenoxy, pyridyloxy, halo-substituted-phenoxy or -pyridyloxy, trifluoromethyl-substituted-phenoxy or -pyridyloxy, C₁ -C₄ alkyloximinomethyl, benzyloximinomethyl, 1-(C₁ -C₄ alkyl)oximinoethyl and 1-benzyloximinoethyl;

Y is hydrogen, halogen, nitro, cyano, perhalomethyl, difluoromethyl, pentafluoroethyl, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, trifluoromethylthio, trifluoromethoxy, tetrafluoroethoxy, methylsulfonyl and trifluoromethylsulfonyl;

Z is hydrogen or fluoro if Y is hydrogen, or hydrogen if Y is other than hydrogen;

R₁ is hydrogen, methyl, ethyl or chloromethyl;

A is oxygen, sulfur, ##STR4## in which R₃ and R₄ are independently hydrogen, methyl or methoxy; and

R₂ is C₁ -C₆ alkyl; carbo(C₁ -C₆)-alkoxy; carbo(C₁ -C₆)alkoxy(C₁ -C₂ alkylene); C₁ -C₄ haloalkyl if m is 1; C₂ -C₄ haloalkyl if m is 0; C₁ -C₅ alkoxy; C₃ -C₆ cycloalkyl optionally substituted by up to 2 methyl groups; C₂ -C₆ alkenyl; phenyl; substituted phenyl in which the substituents are C₁ -C₄ alkyl, halogen, trifluoromethyl, nitro, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, or cyano; phenoxy; halosubstituted phenoxy; styryl; p-chlorophenylsulfonyl; C₂ -C₄ haloalkylcarbonyl; naphthyl; benzoyl; halosubstituted benzoyl; a polycyclic aliphatic group having from 6 to 12 carbon atoms; amino; mono- or di-(C₁ -C₄)alkylamino; C₃ -C₈ alkynyl; cyano; benzyl; or a saturated or unsaturated heterocyclic ring containing from 5 to 6 atoms including from 1 to 2 hetero atoms selected from oxygen and sulfur, optionally substituted by from 1 to 3 methyl groups and/or from 1 to 2 oxo groups; and

m is 0 or 1;

provided that:

(a) when A is --NH-- and R₂ is phenyl or substituted phenyl, then W is oxygen; and

(b) when A is oxygen and R₂ is substituted phenyl, the substituents on the phenyl ring are not meta-directing electron-withdrawing groups; and

(c) when R₂ is cyano or C₃ -C₈ alkynyl and m is 1, then A is --CH₂ --.

The term "alkyl" refers to straight and branched chain acyclic hydrocarbyl moieties having the number of carbon atoms associated with that term whenever used (i.e., by itself or as part of the definition of another moiety, e.g., "haloalkyl", "alkylthio," etc.). Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and the various pentyl, hexyl, etc. moieties. The term "iso-C₅ H₁₁ " (isoamyl or isopentyl) designates the group 3-methylbutyl. The term "sec-C₅ H₁₁ " designates the 2-pentyl group.

The term "carboalkoxy" refers to moieties having the structure ##STR5## in which A represents an alkyl group of the specified number of carbon atoms.

Examples of such group include carbomethoxy, carboethoxy and the like.

The terms "alkenyl" and "alkynyl" refer to straight and branched chain mono- or polyunsaturated acyclic hydrocarbyl moieties with the number of carbon atoms as specified. Examples of such groups include vinyl, allyl, isopropenyl, isobutenyl, propargyl and the like.

The term "cycloalkyl" refers to saturated cyclic hydrocarbyl moieties having the specified number of carbon atoms and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl.

The term "haloalkyl" refers to an alkyl group having the indicated number of carbon atoms, substituted by one or more halogen atoms, which may be the same or different. When unspecified, the term "haloalkyl" is meant to refer to alkyl groups ranging from monohaloalkyl to fully substituted haloalkyl groups. Examples of haloalkyl groups include chloromethyl, dichloromethyl, difluoromethyl, trifluoromethyl, 2-chloroethyl, pentafluoroethyl, heptafluoropropyl, 3-chloropropyl, 2,2,2-trifluoro-1-methylethyl, and the like. The term "perhalomethyl" refers to fully halogenated methyl groups such as trifluoromethyl, trichloromethyl, dichlorofluoromethyl and the like.

The heterocyclic rings included in the definition of R₂ may be saturated or may be mono- or di-unsaturated. Such rings will contain one or two oxygen or sulfur atoms, for instance, furanyl, tetrahydrofuranyl, tetrahydropyranyl, 1,3-dioxolanyl, 1,3-dioxanyl, 1,4-dioxanyl, tetrahydrothienyl, and the like, optionally substituted with from 1 to 3 methyl groups. In addition or alternatively to the methyl substitution, the or two oxygen or sulfur atoms, for instance, furanyl, tetrahydrofuranyl, tetrahydropyranyl, 1,3-dioxolanyl, 1,3-dioxanyl, 1,4-dioxanyl, tetrahydrothienyl, and the like, optionally substituted with from 1 to 3 methyl groups. In addition or alternatively to the methyl substitution, the heterocyclic ring may have one or more oxygen atoms doubly bonded to carbon or sulfur atoms in the ring.

Polycyclic aliphatic groups include both bi- and tricyclic groups having the indicated number of carbon atoms, for instance the tricyclic adamantyl group.

When it is indicated that a phenyl ring may be di- or further substituted, the substituents may be the same or different, and are selected from the specified groups. When no specific position of substitution is mentioned on a phenyl ring, it is intended that the substituent or substituents may be substituted at any position on the ring.

However, when A is oxygen, substituents on a phenyl ring for R₂ should not be meta-directing electron-withdrawing groups such as nitro or cyano. In such case, the phenyl ring may be substituted with ortho/paradirecting groups (even of the electron-withdrawing type) such as halo, alkoxy and alkyl.

As used herein, the term "herbicide" means a compound or composition which adversely controls or modifies the growth of plants. By the term "herbicidally effective amount" is meant any amount of such compound or composition which causes an adverse modifying effect upon the growth of plants. By "plants" is meant germinant seeds, emerging seedlings and established vegetation, including roots and above-ground portions. Such controlling or modifying effects include all deviations from natural development, such as killing, retardation, defoliation, desiccation, regulation, stunting, tillering, leaf burn, dwarfing, and the like.

The compounds of this invention have been found to be active herbicides, possessing pre- and/or post-emergence herbicidal activity against various types of weeds including broadleaf and grassy weeds. As mentioned below, some of the compounds demonstrate good control of weeds in certain crops such as rice, wheat, corn and cotton.

Therefore this invention also relates to a method for controlling undesirable vegetation in general comprising applying to a locus where control of such vegetation is desired, either prior or subsequent to the emergence of such vegetation, a herbicidally effective amount of a compound as described herein. In another aspect, the invention also relates to herbicidal compositions comprising a herbicidally effective amount of a compound as described herein, together with an inert diluent or carrier suitable for use with herbicides.

The compounds of this invention can be prepared by reaction of a 2-iminothiazolidine with an acylating agent, an isocyanate (when W is oxygen and A is --NH--) or an isothiocyanate (when W is sulfur and A is --NH--) in the presence of a suitable base according to the reaction ##STR6## in which Hal stands for halogen, preferably chlorine or bromine. When an acylating agent is used in this step, the reaction is preferably carried out at a temperature of from about 0° to about 10° C. When an isocyanate or an isothiocyanate is used, the reaction is generally conducted at room temperature under nitrogen or other suitable inert gas.

The starting 2-iminothiazolidines may be prepared according to any of several methods as convenient. For instance, U.S. Pat. No. 4,565,083 discloses several methods for production of compounds of this general type, including cyclization of an isothiocyanate and reaction of an iminothiazolidine with a substituted phenyl fluoride. According to another process, as described in Application Ser. No. 214349 of Frank X. Woolard and Charles Kezerian, entitled "Process for Production of 2-Iminothiazolidines and Oxazolidines", filed concurrently herewith, these intermediates can be prepared by reacting an appropriately substituted phenyl cyanamide in a suitable solvent (for instance toluene or methyl ethyl ketone) with an episulfide and a base according to the reaction ##STR7##

The starting phenyl cyanamides can be made by a number of different methods. These compounds are known in the literature. See, for example, Organic Synthesis, Vol. IV, p. 172 and German Patent Application (OLS) 3,538,128.

The examples which follow illustrate production of compounds of this procedure.

EXAMPLE 1 Preparation of 2-(4-Fluorobenzoylimino)-3-(3-trifluoromethyl)phenyl-5-ethylthiazolidine (Compound 12 herein)

3-Trifluoromethylphenyl cyanamide (62.24 g, 0.334 mol), 1,2-butane episulfide (29.48 g, 0.334 mol) and K₂ CO₃ (46.16 g, 0.334 mole)along with 500 ml methyl ethyl ketone were combined in a flask equipped with a heating mantle, mechanical stirrer, an reflux condenser equipped with a nitrogen bubbler. The solution was stirred and heated to reflux temperature. After 3 hours, the solution was cooled to room temperature, filtered and the solvent removed in vacuo to give a cloudy oil. The oil was taken up in 300 ml ethyl acetate and washed twice with 200 ml H₂ O, and 150 ml saturated NaCl. It was then dried (over Na₂ SO₄) and the solvent removed in vacuo to give 73.99 g (81%) of product as a clear yellow oil. The product was identified spectroscopically as 2-imino-3-(3-trifluoromethyl)phenyl-5-ethyl thiazolidine.

To a flask equipped with a magnetic stirrer, thermometer and pressure equalizing addition funnel carrying a nitrogen bubbler, was added 2.50 g (9.1 mmol) of the thiazolidine prepared above, 1.27 ml (9.1 mmol) triethylamine and 25 ml of benzene. The solution was stirred and cooled to10° C. Thereafter 1.07 (9.1 mmol) of p-fluorobenzoyl chloride in 10 ml of benzene was added dropwise over a five minute period while the solution was stirred under nitrogen until the addition was complete. The suspension was then washed over 50 ml 3% aqueous HCl, twice with 50 ml water, with 50 ml brine, dried (over MgSO₄) and the solvent removed in vacuo to give 3.62 g (100%) of product as a thick pale yellow oil. The oil was identified spectroscopically as the subject compound.

EXAMPLE 2 Preparation of 2-(N-Isopropylcarbamoyl)imino-3-(3-trifluoromethyl)phenyl-5-ethyl thiazolidine (Compound 3 herein)

Two grams (7.3 mmol) of 2-imino-3-(3-trifluoromethyl)phenyl-5-ethylthiazolidine prepared in accordance with the method described in paragraph (1) of Example 1 and 0.72 ml (0.62 g, 7.3 mmol) of isopropyl isocyanate were combined in 30 ml of acetonitrile and stirred overnight under nitrogen at room temperature. Several more drops of the isocyanate were added and the solution stirred for an additional 1.5 hour. The solvent was removed in vacuo to give a yellow-orange syrup that was chromatographed on a silica column in 1:1 ethyl acetate/hexanes to yield 1.41 g (54% of theoretical yield) of product as a caramel colored syrup. The structure was confirmed spectroscopically.

EXAMPLE 3 Preparation of 2-(Isopropoxycarbonyl)imino-3-(3-trifluoromethyl)phenyl-5-ethyl thiazolidine (Compound 4 herein)

To a 500 ml, round-bottomed flask equipped with a stirrer, thermometer, andpressure equalizing addition funnel carrying a nitrogen bubbler was added 18.30 g (66.7 mmol) of 2-imino-3-(3-trifluoromethyl)phenyl-5-ethylthiazolidine prepared in accordance with the method described in paragraph (1) of Example 1 and 200ml of benzene, plus 5.41 ml (5.28 g, 66.7 mmol) pyridine. The contents werecooled to 5° C. with stirring. Thereafter, 7.60 ml (66.7 mmol) of isopropyl chloroformate in 50 ml of benzene was then added dropwise at such a rate that the temperature did not rise above 10° C. (about 18 min.). The stirring was then continued at 5° C. for 0.5 nhour atwhich time gas chromatographic analysis showed the reaction to be complete.The reaction suspension was poured into a separation funnel and washed with4×125 ml of water, 1×125 ml 3% HCl, 1×125 ml brine, dried(over MgSO₄) and the solvent removed in vacuo to give 23.18 g (97%) ofproduct was a clear light yellow-orange oil. The structure was confirmed spectroscopically.

Table 1 depicts representative compounds of this invention.

                                      TABLE I                                      __________________________________________________________________________      ##STR8##                                                                      Cmpd.                                Physical Constant                         No. W X  Y Z R.sub.1                                                                              A     R.sub.2     m.p. °C. or                        __________________________________________________________________________                                          n.sub.D.sup.30                            1   O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   i-C.sub.4 H.sub.9                                                                          thick syrup                               2   O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    CH.sub.3    150.0-153.0                               3   O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    i-C.sub.3 H.sub.7                                                                          waxy solid                                4   O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     i-C.sub.3 H.sub.7                                                                          thick syrup                               5   O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      S     i-C.sub.3 H.sub.7                                                                          102.0-104.0                               6   O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             COOC.sub.2 H.sub. 5                                                                        thick syrup                               7   O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CH.sub.3    1.5415                                    8   O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CH.sub.2 Cl thick syrup                               9   O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CHCl.sub.2  thick syrup                               10  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             OCH.sub.3   thick syrup                               11  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)                                                                                   ##STR9##   waxy solid                                12  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   2-FC.sub.6 H.sub.4                                                                         thick syrup                               13  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   4-FC.sub.6 H.sub.4                                                                         waxy solid                                14  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     CH.sub.3    waxy solid                                15  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     C.sub.2 H.sub.5                                                                            1.5336                                    16  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CHCH.sub.2  thick syrup                               17  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   C.sub.2 H.sub.5                                                                            1.5345                                    18  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CHClCH.sub.3                                                                               1.5379                                    19  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CH.sub.2 CH.sub.2 Cl                                                                       1.5393                                    20  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CHClCH.sub.2 Cl                                                                            1.5512                                    21  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CHBrCH.sub.2 Br                                                                            thick syrup                               22  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   C(CH.sub.3)CH.sub.2                                                                        thick syrup                               23  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CHCHCH.sub.3                                                                               1.5559                                    24  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CHC(CH.sub.3).sub.2                                                                        waxy solid                                25  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CH.sub.2 CHCH.sub.2                                                                        1.5746                                    26  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O                                                                                     ##STR10##  thick syrup                               27  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     CH(CH.sub.3)COOCH.sub.3                                                                    thick syrup                               28  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             OC.sub.6 H.sub.5                                                                           thick syrup                               29  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   3-FC.sub.6 H.sub.4                                                                         waxy solid                                30  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CCl.sub.3   waxy solid                                31  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   sec-C.sub.4 H.sub.9                                                                        1.5242                                    32  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   t-C.sub.4 H.sub.9                                                                          81.0-86.5                                 33  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CH.sub.2 C(CH.sub.3).sub.3                                                                 1.5191                                    34  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CH(C.sub.2 H.sub.5).sub.2                                                                  1.5255                                    35  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CH.sub.2 CH(CH.sub.3)CF.sub.3                                                              1.5003                                    36  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   COOC.sub.2 H.sub.5                                                                         waxy solid                                37  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)                                                                                   ##STR11##  waxy solid                                38  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                              ##STR12##  1.5285                                    39  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CHCHC.sub.6 H.sub.5 (trans)                                                                waxy solid                                40  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH(CH.sub.3)                                                                         OC.sub.6 H.sub.5                                                                           thick syrup                               41  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             O(4-ClC.sub.6 H.sub.4)                                                                     thick syrup                               42  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   2-CH.sub.3C.sub.6 H.sub.4                                                                  90.0-95.0                                 43  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   2-ClC.sub.6 H.sub.4                                                                        97.0-102.0                                44  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   3-ClC.sub.6 H.sub.4                                                                        thick syrup                               45  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   4-ClC.sub.6 H.sub.4                                                                        88.0-95.0                                 46  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   3-CF.sub.3C.sub.6 H.sub.4                                                                  62.0-68.0                                 47  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   2,6-FC.sub.6 H.sub.3                                                                       thick syrup                               48  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CH.sub.2 Br thick syrup                               49  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   n-C.sub.3 H.sub.7                                                                          1.5400                                    50  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   C(CH.sub.3).sub.2 CH.sub.2 Cl                                                              65.0-69.0                                 51  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CH(CH.sub.3)C.sub.3 H.sub.7                                                                1.5315                                    52  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          1.5238                                    53  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   i-C.sub.5 H.sub.11                                                                         1.5251                                    54  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   CHCHC.sub.2 H.sub.5 (trans)                                                                1.5451                                    55  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)                                                                                   ##STR13##  1.5438                                    56  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   N(C.sub.2 H.sub.5).sub.2                                                                   71.0-75.5                                 57  S CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   N(CH.sub.3).sub.2                                                                          71.0-78.5                                 58  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   NH.sub.2    foam                                      59  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   COOCH.sub.3 75.5-84.0                                 60  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     CH.sub.2 CCl.sub. 3                                                                        thick syrup                               61  O Cl H F C.sub.2 H.sub.5                                                                      O     i-C.sub.3 H.sub.7                                                                          thick syrup                               62  O CN H H C.sub.2 H.sub.5                                                                      O     i-C.sub.3 H.sub.7                                                                          thick syrup                               63  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     n-C.sub.3 H.sub.7                                                                          1.5196                                    64  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     CH.sub.2 CH.sub.2 Cl                                                                       1.5426                                    65  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     CH.sub.2 CH(CH.sub.3).sub.2                                                                1.5170                                    66  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     CH.sub.2 CHCH.sub.2                                                                        1.5365                                    67  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     n-C.sub.4 H.sub.9                                                                          1.5220                                    68  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     CH.sub.2 CH.sub.2 CH.sub.2 Cl                                                              1.5355                                    69  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             O2,4-ClC.sub.6 H.sub.3                                                                     thick syrup                               70  O CF.sub.3                                                                          H F C.sub.2 H.sub.5                                                                      O     C.sub.2 H.sub.5                                                                            thick syrup                               71  O Cl H H C.sub.2 H.sub.5                                                                      O     C.sub.2 H.sub.5                                                                            1.5737                                    72  O CF.sub.3                                                                          H F C.sub.2 H.sub. 5                                                                     O     i-C.sub.3 H.sub.7                                                                          thick syrup                               73  O Cl H H C.sub.2 H.sub.5                                                                      O     i-C.sub.3 H.sub.7                                                                          1.5592                                    74  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     CCl.sub.3   65.0-65.0                                 75  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      S     C.sub.2 H.sub.5                                                                            99.0-104.5                                76  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    C.sub.2 H.sub.5                                                                            thick syrup                               77  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    t-C.sub.4 H.sub.9                                                                          94.0-99.0                                 78  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    n-C.sub.3 H.sub.7                                                                          waxy solid                                79  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    CH.sub.2 CHCH.sub.2                                                                        thick syrup                               80  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    n-C.sub.4 H.sub.9                                                                          67.0-79.0                                 81  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    2-FC.sub.6 H.sub.4                                                                         118.0-130.0                               82  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    3-FC.sub.6 H.sub.4                                                                         101.5-110.0                               83  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    4-FC.sub.6 H.sub.4                                                                         121.5-128.0                               84  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     sec-C.sub.4 H.sub.9                                                                        thick syrup                               85  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     CH(C.sub.2 H.sub.5).sub.2                                                                  67.0-73.0                                 86  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    COCH.sub.2 Cl                                                                              102.0-107.0                               87  S CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    t-C.sub.4 H.sub.9                                                                          107.0-115.0                               88  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      S     t-C.sub.4 H.sub.9                                                                          119.0-125.0                               89  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      S     CH.sub.3    103.5-107.0                               90  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      S     n-C.sub.3 H.sub.7                                                                          60.0-64.0                                 91  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      S     CH.sub.2 CH.sub.2 Cl                                                                       thick syrup                               92  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      S     sec-C.sub.4 H.sub.9                                                                        99.0-106.5                                93  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      S     i-C.sub.4 H.sub.9                                                                          64.0-72.0                                 94  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      S     n-C.sub.4 H.sub.9                                                                          thick syrup                               95  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      S     CH.sub.2 CH.sub.2 CH.sub.2 Cl                                                              thick syrup                               96  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      S     CH.sub.2 CHClCH.sub.2 Cl                                                                   thick syrup                               97  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             3-CF.sub.3C.sub.6 H.sub.4                                                                  thick syrup                               98  O NO.sub.2                                                                          H H C.sub.2 H.sub.5                                                                      O     i-C.sub.3 H.sub.7                                                                          thick syrup                               99  O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      S     i-C.sub.5 H.sub.11                                                                         1.5566                                    100 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      S     CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                     51.0-54.0                                 101 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      S     n-C.sub.5 H.sub.11                                                                         1.5549                                    102 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   2-NO.sub.2C.sub.6 H.sub.4                                                                  106.0-120.0                               103 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   2-CH.sub.3 OC.sub.6 H.sub.4                                                                113.0-115.0                               104 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   3,4,5-CH.sub.3 OC.sub.6 H.sub.2                                                            thick syrup                               105 O NO.sub.2                                                                          H H C.sub.2 H.sub.5                                                                      O     C.sub.2 H.sub.5                                                                            waxy solid                                106 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub. 2                                                                            C.sub.6 H.sub.5                                                                            60.0-63.0                                 107 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             4-FC.sub.6 H.sub.4                                                                         waxy solid                                108 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     C.sub.6 H.sub.5                                                                            thick syrup                               109 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     2,4,5-ClC.sub.6 H.sub.2                                                                    thick syrup                               110 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     4-[C(CH.sub.3).sub.3 ]C.sub.6 H.sub.4                                                      waxy solid                                111 S CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    C.sub.2 H.sub.5                                                                            160.5-162.0                               112 S CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    2-FC.sub.6 H.sub.4                                                                         112.0-116.0                               113 S CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    4-FC.sub.6 H.sub.4                                                                         161.0-166.0                               114 S CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    3-FC.sub.6 H.sub.4                                                                         159.0-162.5                               115 S CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    n-C.sub.3 H.sub.7                                                                          153.0-156.0                               116 S CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    i-C.sub.3 H.sub.7                                                                          130.0-135.0                               117 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     cyclopentyl thick syrup                               118 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             2-ClC.sub.6 H.sub.4                                                                        thick syrup                               119 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             3-ClC.sub.6 H.sub.4                                                                        thick syrup                               120 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             4-ClC.sub.6 H.sub.4                                                                        thick syrup                               121 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             3,4-ClC.sub.6 H.sub.3                                                                      thick syrup                               122 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             3-FC.sub.6 H.sub.4                                                                         1.5596                                    123 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             2-FC.sub.6 H.sub.4                                                                         thick syrup                               124 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             4-CF.sub.3C.sub.6 H.sub.4                                                                  waxy solid                                125 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             2-CF.sub.3C.sub.6 H.sub.4                                                                  thick syrup                               126 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             4-NO.sub.2C.sub.6 H.sub.4                                                                  76.0-91.0                                 127 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             3-CH.sub.3 OC.sub.6 H.sub.4                                                                1.5574                                    128 O CF.sub. 3                                                                         H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             4-CH.sub.3 OC.sub.6 H.sub.4                                                                1.5574                                    129 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH(OCH.sub.3)                                                                        C.sub.6 H.sub.5                                                                            waxy solid                                130 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   α-naphthyl                                                                           thick syrup                               131 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    COC.sub.6 H.sub.5                                                                          108.0-120.0                               132 S CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    COC.sub.6 H.sub.5                                                                          thick syrup                               133 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    CH.sub.2 CH.sub.2 Cl                                                                       thick syrup                               134 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      O     t-C.sub.4 H.sub.9                                                                          100.0-105.0                               135 S CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    2-ClC.sub.6 H.sub.4                                                                        85.0-95.0                                 136 S CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    3-ClC.sub.6 H.sub.4                                                                        126.0-132.0                               137 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    3-ClC.sub.6 H.sub.4                                                                        thick syrup                               138 S CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    3-CF.sub.3C.sub.6 H.sub.4                                                                  112.0-119.0                               139 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    2-CH.sub.3 OC.sub.6 H.sub.4                                                                105.0-111.0                               140 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    3-CH.sub.3 OC.sub.6 H.sub.4                                                                thick syrup                               141 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    3-CH.sub.3 SC.sub.6 H.sub.4                                                                glassy solid                              142 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    2,5-FC.sub.6 H.sub.3                                                                       thick syrup                               143 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      S     4-ClC.sub.6 H.sub.4 CH.sub.2                                                               waxy solid                                144 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.4                                                                      COOC.sub.2 H.sub.5                                                                         1.5285                                    145 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      (-)   2-BrC.sub.6 H.sub.4                                                                        82.0-89.0                                 146 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             2-CH.sub.3C.sub.6 H.sub.4                                                                  thick syrup                               147 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             2-OCH.sub.3C.sub.6 H.sub.4                                                                 thick syrup                               148 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             2-NO.sub.2C.sub.6 H.sub.4                                                                  100.0-117.0                               149 S CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    2-ClC.sub.6 H.sub.4 CO                                                                     thick syrup                               150 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    4-ClC.sub.6 H.sub.4 SO.sub.2                                                               glassy solid                              151 S CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    n-C.sub.4 H.sub.9                                                                          129.0-138.0                               152 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      --                                                                                    ##STR14##  waxy solid                                153 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      --                                                                                    ##STR15##  thick syrup                               154 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                              ##STR16##  1.5670                                    155 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             2,4-ClC.sub.6 H.sub.4                                                                      thick syrup                               156 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             3-NO.sub.2C.sub.6 H.sub.4                                                                  95.0-103.0                                157 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             3-CH.sub.3C.sub.6 H.sub.4                                                                  waxy solid                                158 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             2,6-FC.sub.6 H.sub.3                                                                       thick syrup                               159 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             2,6-ClC.sub.6 H.sub.3                                                                      waxy solid                                160 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    CH.sub.2 COOC.sub.2 H.sub.5                                                                92.0-99.0                                 161 S CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      NH    adamantyl   waxy solid                                162 O CF.sub.3                                                                          H H CONCH.sub.3                                                                          CH.sub.3                                                                             C.sub.2 H.sub.5                                                                            thick syrup                               163 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             2,3-(CH.sub.3 O)C.sub.6 H.sub.3                                                            thick syrup                               164 O CF.sub.3                                                                          H H CH.sub.2 Cl                                                                          O     i-C.sub.3 H.sub.7                                                                          waxy solid                                165 O CF.sub.3                                                                          H H CH.sub.3                                                                             O     i-C.sub.3 H.sub.7                                                                          thick syrup                               166 O CF.sub.3                                                                          H F C.sub.2 H.sub.5                                                                      (-)                                                                                   ##STR17##  waxy solid                                167 O CF.sub.3                                                                          H F C.sub.2 H.sub.5                                                                      (-)                                                                                   ##STR18##  waxy solid                                168 O CF.sub.3                                                                          H H C.sub.2 H.sub.5                                                                      CH.sub.2                                                                             2,3-FC.sub.6 H.sub.3                                                                       thick syrup                               169 O CF.sub.3                                                                          H F C.sub.2 H.sub.5                                                                      (-)                                                                                   ##STR19##  thick syrup                               170 O CF.sub.3                                                                          H H CH.sub.2 Cl                                                                          (-)   i-C.sub.4 H.sub.9                                                                          thick syrup                               171 O CF.sub.3                                                                          H H CH.sub.2 Cl                                                                          NH    i-C.sub.3 H.sub.7                                                                          thick syrup                               172 O CF.sub.3                                                                          H H CH.sub.2 Cl                                                                          S     i-C.sub.3 H.sub.7                                                                          waxy solid                                173 O CF.sub.3                                                                          H H CH.sub.3                                                                             (-)   i-C.sub.4 H.sub.9                                                                          thick syrup                               __________________________________________________________________________     (-) Indicates an electron bond, i.e., m = 0.                              

HERBICIDAL ACTIVITY TESTS

Compounds in Table 1 were tested for herbicidal activity as follows.

The herbicidal effect is observed by comparing the extent of weed control in test flats treated with the compounds against that occurring in similarnon-treated control flats. All were applied at 4.0 lb/A (4.48 kg/ha) to pre-emergence and post-emergence screening flats. An 80 gal/A (748.3 l/ha)spray volume was utilized. Post-emergence flats were seeded 12 days prior to treatment. Pre-emergence flats were seeded one day prior to treatment. Overhead watering of pre-emergence flats and soil surface watering of post-emergence flats, so as to avoid wetting the foliage, were carried outfor the duration of the test.

Weed seeds were planted in a flat at a seed depth of 0.5 inch (1.3 cm). Soil for flats was prepared using loam soil fortified with 17-17-17 fertilizer (N-P₂ O₅ -K₂ O on a weight basis) and Captan 80Wfungicide. The test weeds were as follows:

    ______________________________________                                         COMMON NAME    SCIENTIFIC NAME ABR                                             ______________________________________                                         green foxtail  Setaria viridis SETVI                                           watergrass     Echinochloa crusgalli                                                                          ECHCG                                           wild oat       Avena fatua     AVEFA                                           annual morningglory                                                                           Ipomoea purpurea                                                                               PHBPU                                           velvetleaf     Abutilon theophrasti                                                                           ABUTH                                           wild mustard   Brassica kaber  SINAR                                           yellow nutsedge                                                                               Cyperus esculentus                                                                             CYPES                                           ______________________________________                                    

The spray solutions were prepared by dissolving 240 mg of test compound in 20 ml of acetone containing 1% polyoxyethylene sorbitan monolaurate emulsifier, then adding 20 ml of water to the resulting solution. The stock solutions were applied using a linear spray table. Pre-emergence flats are raised to the level of the post-emergence foliage canopy by setting the flats on a wooden block.

In both pre- and post-emergent testing, the degree of weed control was visually assessed, approximately 18 days after treatment, and recorded as percentage control compared to the growth of the same species in an untreated check flat of the same age. The rating scale ranges from 0 to 100%, where 0 equals no effect with plant growth equal to the untreated control, and 100 equals complete kill.

The results are listed in the Table below.

                                      TABLE II                                     __________________________________________________________________________     GREENHOUSE HERBICIDE TEST RESULTS                                              Application                                                                    Cmpd.                                                                              Rate     Percent Injury                                                    No. (lb/A)                                                                             Method                                                                              SETVI                                                                              ECHCG                                                                               AVEFA                                                                               PHPBU                                                                               ABUTH                                                                               SINAR                                                                               CYPES                                __________________________________________________________________________     1   4.00                                                                               PES  100 100  90   100  100  100  30                                       4.00                                                                               POS  100 80   80   80   80   70   80                                   2   4.00                                                                               PES  100 100  80   100  100  100  70                                       4.00                                                                               POS  95  85   60   75   75   80   80                                   3   4.00                                                                               PES  100 100  80   100  100  100  70                                       4.00                                                                               POS  90  80   70   50   50   80   80                                   4   4.00                                                                               PES  100 90   100  100  100  100  80                                       4.00                                                                               POS  100 80   80   80   90   50   80                                   5   4.00                                                                               PES  100 70   75   100  75   100  0                                        4.00                                                                               POS  80  50   50   90   90   60   0                                    6   4.00                                                                               PES  10  10   0    5    5    20   0                                        4.00                                                                               POS  10  20   10   10   80   80   0                                    7   4.00                                                                               PES  100 40   10   0    0    100  0                                        4.00                                                                               POS  20  20   20   0    30   80   0                                    8   4.00                                                                               PES  100 30   0    10   0    100  0                                        4.00                                                                               POS  20  20   0    10   80   100  0                                    9   4.00                                                                               PES  100 30   10   10   80   100  0                                        4.00                                                                               POS  20  20   20   10   80   100  0                                    10  4.00                                                                               PES  100 100  85   60   100  100  60                                       4.00                                                                               POS  100 90   80   40   80   100  75                                   11  4.00                                                                               PES  100 100  100  100  100  100  80                                       4.00                                                                               POS  100 85   85   100  100  100  80                                   12  4.00                                                                               PES  100 100  100  100  100  100  0                                        4.00                                                                               POS  50  50   50   60   85   90   0                                    13  4.00                                                                               PES  100 30   10   100  100  100  0                                        4.00                                                                               POS  100 50   50   100  90   100  0                                    14  4.00                                                                               PES  100 100  100  100  100  100  60                                       4.00                                                                               POS  100 100  100  100  85   100  20                                   15  4.00                                                                               PES  100 100  95   100  100  100  60                                       4.00                                                                               POS  100 80   80   80   80   100  75                                   16  4.00                                                                               PES  100 10   10   40   100  100  0                                        4.00                                                                               POS  0   20   0    20   30   80   0                                    17  4.00                                                                               PES  100 100  80   10   90   100  0                                        4.00                                                                               POS  100 30   10   10   80   90   0                                    18  4.00                                                                               PES  100 100  20   90   100  100  0                                        4.00                                                                               POS  20  20   20   100  80   100  0                                    19  4.00                                                                               PES  100 100  100  100  100  100  0                                        4.00                                                                               POS  100 40   40   30   80   90   0                                    20  4.00                                                                               PES  100 20   10   20   95   100  0                                        4.00                                                                               POS  10  10   10   10   80   90   0                                    21  4.00                                                                               PES  80  10   0    10   80   100  0                                        4.00                                                                               POS  0   0    0    10   10   100  0                                    22  4.00                                                                               PES  100 100  50   80   100  100  0                                        4.00                                                                               POS  100 50   50   100  85   100  30                                   23  4.00                                                                               PES  100 100  100  100  100  100  0                                        4.00                                                                               POS  100 80   80   80   80   90   70                                   24  4.00                                                                               PES  100 100  100  100  100  100  30                                       4.00                                                                               POS  100 85   90   100  90   100  75                                   25  4.00                                                                               PES  100 100  90   100  100  100  0                                        4.00                                                                               POS  100 80   80   100  90   100  30                                   26  4.00                                                                               PES  100 100  100  100  100  100  80                                       4.00                                                                               POS  100 90   80   100  95   100  80                                   27  4.00                                                                               PES  100 50   50   100  100  100  10                                       4.00                                                                               POS  80  50   50   100  100  100  50                                   28  4.00                                                                               PES  100 20   10   20   20   100  0                                        4.00                                                                               POS  0   10   0    40   80   90   0                                    29  4.00                                                                               PES  100 85   80   100  100  100  0                                        4.00                                                                               POS  10  10   10   60   90   100  0                                    30  4.00                                                                               PES  100 80   60   10   100  100  0                                        4.00                                                                               POS  10  10   10   40   40   80   0                                    31  4.00                                                                               PES  100 100  100  100  100  100  0                                        4.00                                                                               POS  90  90   90   80   90   90   10                                   32  4.00                                                                               PES  100 100  100  100  100  100  10                                       4.00                                                                               POS  100 100  90   80   80   100  0                                    33  4.00                                                                               PES  100 100  100  100  100  100  20                                       4.00                                                                               POS  100 90   90   80   80   100  70                                   34  4.00                                                                               PES  100 100  100  100  100  100  10                                       4.00                                                                               POS  100 80   80   80   80   100  30                                   35  4.00                                                                               PES  100 100  100  100  100  100  10                                       4.00                                                                               POS  100 90   90   80   80   100  60                                   36  4.00                                                                               PES  100 20   10   30   70   100  0                                        4.00                                                                               POS  10  10   10   20   20   80   0                                    37  4.00                                                                               PES  100 100  100  100  100  100  0                                        4.00                                                                               POS  50  50   50   60   60   80   20                                   38  4.00                                                                               PES  100 100  95   100  100  100  0                                        4.00                                                                               POS  100 80   80   80   80   100  20                                   39  4.00                                                                               PES  100 50   20   20   70   100  0                                        4.00                                                                               POS  20  20   20   40   60   80   0                                    40  4.00                                                                               PES  100 75   30   40   75   100  0                                        4.00                                                                               POS  10  0    0    40   60   80   0                                    41  4.00                                                                               PES  100 80   30   100  100  100  0                                        4.00                                                                               POS  50  10   0    100  100  100  0                                    42  4.00                                                                               PES  100 80   70   60   100  100  0                                        4.00                                                                               POS  50  50   50   40   60   60   0                                    43  4.00                                                                               PES  100 80   60   100  100  100  0                                        4.00                                                                               POS  50  50   50   30   50   80   0                                    44  4.00                                                                               PES  100 50   30   80   100  100  0                                        4.00                                                                               POS  30  30   30   40   80   80   0                                    45  4.00                                                                               PES  100 60   30   80   100  100  0                                        4.00                                                                               POS  30  30   30   30   30   80   0                                    46  4.00                                                                               PES  100 40   30   70   85   100  0                                        4.00                                                                               POS  30  80   30   60   80   80   0                                    47  4.00                                                                               PES  100 30   10   60   100  100  0                                        4.00                                                                               POS  30  30   30   40   60   80   0                                    48  4.00                                                                               PES  100 20   0    10   0    100  0                                        4.00                                                                               POS  30  30   30   60   60   80   0                                    49  4.00                                                                               PES  100 100  95   95   100  100  0                                        4.00                                                                               POS  80  30   60   40   80   80   0                                    50  4.00                                                                               PES  100 100  80   100  100  100  0                                        4.00                                                                               POS  80  80   60   80   80   80   10                                   51  4.00                                                                               PES  100 100  85   100  100  100  0                                        4.00                                                                               POS  100 80   80   90   85   100  30                                   51  4.00                                                                               PES  100 100  85   100  100  100  0                                        4.00                                                                               POS  100 80   80   90   85   100  30                                   52  4.00                                                                               PES  100 100  30   80   100  100  0                                        4.00                                                                               POS  100 90   80   90   90   90   0                                    53  4.00                                                                               PES  100 100  80   100  100  100  0                                        4.00                                                                               POS  100 90   80   95   100  100  0                                    54  4.00                                                                               PES  100 100  50   75   100  100  0                                        4.00                                                                               POS  100 85   50   85   85   100  0                                    55  4.00                                                                               PES  100 100  95   100  100  100  0                                        4.00                                                                               POS  100 85   80   100  100  100  30                                   56  4.00                                                                               PES  100 100  100  100  100  100  0                                        4.00                                                                               POS  100 90   85   80   80   80   60                                   57  4.00                                                                               PES  100 100  100  100  100  100  30                                       4.00                                                                               POS  100 100  90   85   90   100  70                                   58  4.00                                                                               PES  100 100  90   100  100  100  80                                       4.00                                                                               POS  100 85   80   80   80   100  80                                   59  4.00                                                                               PES  100 0    0    10   10   100  0                                        4.00                                                                               POS  0   10   0    20   30   80   0                                    60  4.00                                                                               PES  100 10   30   0    100  100  0                                        4.00                                                                               POS  10  10   10   20   50   90   0                                    61  4.00                                                                               PES  100 100  100  100  100  100  70                                       4.00                                                                               POS  100 100  100  90   100  90   80                                   62  4.00                                                                               PES  100 100  100  100  100  100  80                                       4.00                                                                               POS  100 100  90   100  100  100  80                                   63  4.00                                                                               PES  100 100  100  100  100  100  30                                       4.00                                                                               POS  100 90   80   90   90   80   70                                   64  4.00                                                                               PES  100 100  80   100  100  100  0                                        4.00                                                                               POS  100 100  80   80   80   80   70                                   65  4.00                                                                               PES  100 100  100  100  100  100  0                                        4.00                                                                               POS  100 90   90   80   95   90   70                                   66  4.00                                                                               PES  100 90   100  100  100  100  50                                       4.00                                                                               POS  100 80   80   60   80   90   80                                   67  4.00                                                                               PES  100 60   40   100  100  100  0                                        4.00                                                                               POS  100 50   50   70   80   90   30                                   68  4.00                                                                               PES  100 80   0    100  100  100  0                                        4.00                                                                               POS  100 50   50   60   80   90   50                                   69  4.00                                                                               PES  100 80   0    100  80   100  0                                        4.00                                                                               POS  10  10   10   100  100  100  0                                    70  4.00                                                                               PES  100 100  100  100  100  100  80                                       4.00                                                                               POS  100 100  95   75   90   100  90                                   71  4.00                                                                               PES  100 100  95   100  20   100  70                                       4.00                                                                               POS  100 100  60   60   80   100  75                                   72  4.00                                                                               PES  100 100  100  100  100  100  80                                       4.00                                                                               POS  100 90   80   80   80   80   80                                   73  4.00                                                                               PES  100 100  100  100  100  100  70                                       4.00                                                                               POS  100 95   95   90   85   100  80                                   74  4.00                                                                               PES  100 90   50   20   20   100  0                                        4.00                                                                               POS  50  50   50   60   60   80   20                                   75  4.00                                                                               PES  100 100  95   100  100  100  0                                        4.00                                                                               POS  80  60   50   40   80   80   0                                    76  4.00                                                                               PES  100 100  100  100  100  100  80                                       4.00                                                                               POS  100 100  100  90   90   100  80                                   77  4.00                                                                               PES  100 100  100  100  100  100  80                                       4.00                                                                               POS  100 100  100  100  100  100  80                                   78  4.00                                                                               PES  100 100  100  100  100  100  70                                       4.00                                                                               POS  100 90   100  80   80   100  80                                   79  4.00                                                                               PES  100 100  100  100  100  100  70                                       4.00                                                                               POS  80  80   80   80   80   80   80                                   80  4.00                                                                               PES  100 100  100  100  100  100  70                                       4.00                                                                               POS  80  70   75   80   80   80   80                                   81  4.00                                                                               PES  100 50   50   100  100  100  0                                        4.00                                                                               POS  50  50   50   20   50   80   0                                    82  4.00                                                                               PES  100 60   40   100  100  100  0                                        4.00                                                                               POS  50  50   50   20   60   80   0                                    83  4.00                                                                               PES  100 30   30   100  100  100  0                                        4.00                                                                               POS  0   0    0    40   80   80   0                                    84  4.00                                                                               PES  100 100  100  100  100  100  80                                       4.00                                                                               POS  100 90   80   80   80   80   80                                   85  4.00                                                                               PES  100 100  90   100  100  100  0                                        4.00                                                                               POS  50  60   50   80   80   80   50                                   86  4.00                                                                               PES  100 100  100  100  100  100  80                                       4.00                                                                               POS  100 80   60   80   80   80   80                                   87  4.00                                                                               PES  100 100  100  100  100  100  70                                       4.00                                                                               POS  100 90   90   80   90   90   80                                   88  4.00                                                                               PES  100 80   75   90   100  100  0                                        4.00                                                                               POS  20  20   20   30   30   50   0                                    89  4.00                                                                               PES  100 100  100  100  100  100  30                                       4.00                                                                               POS  100 80   80   60   80   80   80                                   90  4.00                                                                               PES  100 100  100  100  100  100  0                                        4.00                                                                               POS  80  30   60   60   80   90   20                                   91  4.00                                                                               PES  100 100  90   100  100  100  0                                        4.00                                                                               POS  100 50   50   60   80   80   80                                   92  4.00                                                                               PES  100 30   80   100  100  100  0                                        4.00                                                                               POS  20  20   20   30   50   100  0                                    93  4.00                                                                               PES  100 50   100  100  100  100  0                                        4.00                                                                               POS  80  30   50   60   80   80   0                                    94  4.00                                                                               PES  100 75   90   100  100  100  0                                        4.00                                                                               POS  20  20   20   60   80   80   0                                    95  4.00                                                                               PES  100 20   80   100  100  100  0                                        4.00                                                                               POS  20  30   20   80   80   80   0                                    96  4.00                                                                               PES  100 20   40   100  100  100  0                                        4.00                                                                               POS  20  20   20   40   80   80   0                                    97  4.00                                                                               PES  100 50   40   100  100  100  0                                        4.00                                                                               POS  30  30   20   60   80   80   0                                    98  4.00                                                                               PES  100 100  100  100  100  100  80                                       4.00                                                                               POS  100 80   80   80   80   100  80                                   99  4.00                                                                               PES  100 100  30   100  100  100  0                                        4.00                                                                               POS  20  20   20   40   50   80   0                                    100 4.00                                                                               PES  100 50   30   100  100  100  0                                        4.00                                                                               POS  20  20   20   50   60   100  0                                    101 4.00                                                                               PES  100 20   20   100  80   100  0                                        4.00                                                                               POS  20  0    0    20   50   100  0                                    102 4.00                                                                               PES  20  20   20   40   100  100  0                                        4.00                                                                               POS  50  20   20   30   50   80   0                                    103 4.00                                                                               PES  100 30   20   90   100  100  0                                        4.00                                                                               POS  20  20   20   30   50   100  0                                    104 4.00                                                                               PES  100 0    10   20   20   100  0                                        4.00                                                                               POS  0   0    0    20   30   100  0                                    105 4.00                                                                               PES  100 75   60   10   100  100  30                                       4.00                                                                               POS  100 80   80   40   60   100  80                                   106 4.00                                                                               PES  100 100  90   100  100  100  0                                        4.00                                                                               POS  100 80   80   60   80   100  30                                   107 4.00                                                                               PES  100 100  85   100  100  100  0                                        4.00                                                                               POS  100 60   50   60   60   100  0                                    108 4.00                                                                               PES  100 10   10   10   10   100  0                                        4.00                                                                               POS  0   0    0    10   0    100  0                                    109 4.00                                                                               PES  100 0    0    10   10   100  0                                        4.00                                                                               POS  0   0    0    10   20   80   0                                    110 4.00                                                                               PES  100 10   0    20   30   100  0                                        4.00                                                                               POS  0   0    0    10   10   80   0                                    111 4.00                                                                               PES  100 90   95   100  85   100  0                                        4.00                                                                               POS  100 80   80   60   80   100  80                                   112 4.00                                                                               PES  100 20   20   20   60   100  0                                        4.00                                                                               POS  30  30   30   30   50   80   0                                    113 4.00                                                                               PES  100 10   0    10   10   100  0                                        4.00                                                                               POS  0   0    0    0    0    20   0                                    114 4.00                                                                               PES  100 10   10   20   20   100  0                                        4.00                                                                               POS  10  10   0    30   50   50   0                                    115 4.00                                                                               PES  100 100  70   100  100  100  0                                        4.00                                                                               POS  60  60   60   60   60   100  50                                   116 4.00                                                                               PES  100 100  80   100  100  100  0                                        4.00                                                                               POS  80  90   80   80   60   90   80                                   117 4.00                                                                               PES  100 100  80   100  100  100  0                                        4.00                                                                               POS  80  90   80   80   80   100  80                                   118 4.00                                                                               PES  100 100  80   100  100  100  0                                        4.00                                                                               POS  100 90   70   100  100  100  0                                    119 4.00                                                                               PES  100 100  80   100  100  100  0                                        4.00                                                                               POS  100 90   80   80   80   100  0                                    120 4.00                                                                               PES  100 100  70   100  100  100  0                                        4.00                                                                               POS  100 95   40   60   80   100  0                                    121 4.00                                                                               PES  100 10   10   40   20   100  0                                        4.00                                                                               POS  20  20   20   40   40   80   0                                    122 4.00                                                                               PES  100 100  85   100  100  100  0                                        4.00                                                                               POS  100 100  80   90   90   100  0                                    123 4.00                                                                               PES  100 100  90   100  100  100  0                                        4.00                                                                               POS  100 100  60   100  100  100  20                                   124 4.00                                                                               PES  100 90   20   20   80   100  0                                        4.00                                                                               POS  20  80   20   10   30   100  0                                    125 4.00                                                                               PES  100 30   20   40   60   100  0                                        4.00                                                                               POS  100 30   30   60   50   80   0                                    126 4.00                                                                               PES  100 10   10   10   20   80   0                                        4.00                                                                               POS  20  20   0    20   20   100  0                                    127 4.00                                                                               PES  100 100  75   100  85   100  0                                        4.00                                                                               POS  100 50   30   80   80   100  0                                    128 4.00                                                                               PES  100 100  90   100  100  100  0                                        4.00                                                                               POS  100 100  80   60   80   80   0                                    129 4.00                                                                               PES  100 40   20   40   80   100  0                                        4.00                                                                               POS  100 30   20   60   50   100  0                                    130 4.00                                                                               PES  100 10   10   10   60   100  0                                        4.00                                                                               POS  0   10   0    40   60   100  0                                    131 4.00                                                                               PES  100 10   10   10   75   100  0                                        4.00                                                                               POS  20  30   20   80   80   100  0                                    132 4.00                                                                               PES  100 20   40   40   60   100  0                                        4.00                                                                               POS  90  50   40   85   80   100  50                                   133 4.00                                                                               PES  100 100  20   60   80   85   0                                        4.00                                                                               POS  80  30   30   100  100  85   0                                    134 4.00                                                                               PES  100 100  100  80   100  100  0                                        4.00                                                                               POS  100 30   10   100  100  100  0                                    135 4.00                                                                               PES  100 20   20   60   100  100  0                                        4.00                                                                               POS  70  20   10   40   100  80   0                                    136 4.00                                                                               PES  100 0    0    20   20   50   0                                        4.00                                                                               POS  10  10   0    40   70   80   0                                    137 4.00                                                                               PES  100 20   20   80   80   100  0                                        4.00                                                                               POS  75  20   0    60   80   80   0                                    138 4.00                                                                               PES  100 0    0    0    0    0    0                                        4.00                                                                               POS  10  10   10   20   30   30   0                                    139 4.00                                                                               PES  100 0    10   10   20   20   0                                        4.00                                                                               POS  10  0    0    40   20   50   0                                    140 4.00                                                                               PES  100 30   30   75   100  100  0                                        4.00                                                                               POS  10  10   0    40   80   90   0                                    141 4.00                                                                               PES  100 20   20   75   20   100  0                                        4.00                                                                               POS  20  10   0    100  90   90   0                                    142 4.00                                                                               PES  100 100  75   100  100  100  0                                        4.00                                                                               POS  60  50   30   100  80   80   0                                    143 4.00                                                                               PES  80  0    0    0    0    80   0                                        4.00                                                                               POS  10  10   10   10   80   80   0                                    144 4.00                                                                               PES  20  0    0    0    0    0    0                                        4.00                                                                               POS  0   0    0    20   50   80   0                                    145 4.00                                                                               PES  100 60   30   60   85   100  0                                        4.00                                                                               POS  20  30   20   60   80   80   0                                    146 4.00                                                                               PES  100 100  60   85   90   100  0                                        4.00                                                                               POS  80  50   50   80   80   80   0                                    147 4.00                                                                               PES  100 100  60   70   100  100  0                                        4.00                                                                               POS  80  50   50   80   80   80   0                                    148 4.00                                                                               PES  100 75   20   70   100  100  0                                        4.00                                                                               POS  10  10   10   80   90   90   0                                    149 4.00                                                                               PES  100 95   50   40   90   100  30                                       4.00                                                                               POS  80  50   50   80   80   80   30                                   150 4.00                                                                               PES  80  0    0    0    10   30   0                                        4.00                                                                               POS  0   0    0    20   60   80   0                                    151 4.00                                                                               PES  100 30   30   40   50   100  0                                        4.00                                                                               POS  30  30   20   80   80   80   0                                    152 4.00                                                                               PES  100 100  100  100  100  100  30                                       4.00                                                                               POS  100 80   80   80   80   80   0                                    153 4.00                                                                               PES  100 100  90   100  100  100  30                                       4.00                                                                               POS  100 80   80   80   80   90   30                                   154 4.00                                                                               PES  100 100  85   95   100  100  0                                        4.00                                                                               POS  90  60   50   100  85   100  0                                    155 4.00                                                                               PES  100 85   60   85   100  100  0                                        4.00                                                                               POS  60  40   30   80   80   80   0                                    156 4.00                                                                               PES  100 20   10   40   70   95   0                                        4.00                                                                               POS  20  20   20   60   60   80   0                                    157 4.00                                                                               PES  100 100  80   85   100  100  0                                        4.00                                                                               POS  80  40   30   60   80   80   0                                    158 4.00                                                                               PES  100 100  90   100  100  100  0                                        4.00                                                                               POS  100 100  85   85   90   80   0                                    159 4.00                                                                               PES  100 100  50   80   100  85   0                                        4.00                                                                               POS  80  30   20   80   85   90   20                                   160 4.00                                                                               PES  75  20   0    5    0    0    0                                        4.00                                                                               POS  0   0    0    50   20   100  0                                    161 4.00                                                                               PES  100 30   20   20   60   100  0                                        4.00                                                                               POS  70  30   20   40   80   100  0                                    162 4.00                                                                               PES  100 60   20   20   0    100  0                                        4.00                                                                               POS  100 0    0    30   40   80   0                                    163 4.00                                                                               PES  100 20   10   20   10   100  0                                        4.00                                                                               POS  100 10   10   20   40   85   0                                    164 4.00                                                                               PES  100 100  95   100  100  100  20                                       4.00                                                                               POS  100 100  100  100  100  100  70                                   165 4.00                                                                               PES  100 100  100  100  100  100  80                                       4.00                                                                               POS  100 95   100  80   80   80   80                                   166 4.00                                                                               PES  100 100  100  100  95   100  N                                        4.00                                                                               POS  100 100  100  100  100  100  80                                   167 4.00                                                                               PES  100 100  100  100  100  100  0                                        4.00                                                                               POS  100 100  100  90   95   100  20                                   168 4.00                                                                               PES  100 100  95   100  95   100  0                                        4.00                                                                               POS  100 70   70   80   80   80   10                                   169 4.00                                                                               PES  100 100  95   100  100  100  0                                        4.00                                                                               POS  100 90   100  95   95   100  20                                   170 4.00                                                                               PES  100 100  70   100  95   100  90                                       4.00                                                                               POS  100 90   30   90   90   90   0                                    171 4.00                                                                               PES  100 100  40   100  100  100  20                                       4.00                                                                               POS  100 100  100  95   100  100  80                                   172 4.00                                                                               PES  100 100  30   50   100  100  0                                        4.00                                                                               POS  60  30   20   10   20   80   0                                    173 4.00                                                                               PES  100 100  85   100  100  100  0                                        4.00                                                                               POS  100 90   85   90   90   90   0                                    __________________________________________________________________________

FURTHER HERBICIDAL EVALUATION

Compounds showing good activity in the evaluations described above were submitted for one or more subsequent evaluations involving, for example, different weeds, lower application rates, varying application procedures, and/or selectivity with respect to crops. The weeds employed in these tests included those utilized in the tests just described, as well as a number of others such as one or more species of ryegrass (Lolium), Sorghum, signalgrass (Brachiaria), cocklebur (Xanthium), Sesbania, Cassia,Alopecurus, oats (Avena), bluegrass (Poa), Matricaria, chickweed (Stellaria), bedstraw (Galium), and violet Viola). Crops which were variously employed in these evaluations included cotton (Gossypium hirsutum), soybean (Glycine max), corn (Zea maize), milo (Sorghum bicolor), wheat (Tritium aestivum), sugarbeet (Beta vulgaris), rice (Oryzasativa), carrot (Daucus carota), and barley (Hordeum vulgare).

In summation, compounds submitted for further evaluation showed varying activity depending on the compound and the evaluation employed. Some compounds showed a better activity in controlling grasses, others in controlling broadleaf weeds. Some compounds demonstrated better activity in pre-emergence application, others in post-emergence application. Some compounds demonstrated good activity in nearly all types of application. Some compounds demonstrated good control in tests at application rates ranging as low as 0.06 pound per acre (0.065 kg/ha).

With respect to injury to crops, nearly all compounds tested produced unacceptable injury to sugarbeets even at relatively low levels of application. Some compounds showed good broad-spectrum activity but relatively low selectivity, causing injury to both weeds and crops in the same tests. Other compounds showed varying selectivity to certain crops, particularly cereals, such as wheat, rice and corn, most notably with respect to rice in various methods of application. A number of compounds also demonstrated selectivity in controlling weeds in the presence of cotton.

In practice, a pure compound can be used as a herbicide. However, in general, the compounds are first formulated with one or more inert carriers or diluents suitable for herbicidal use, before being applied.

The compositions or formulations, including a compound as described herein,may exist in any one of a number of solid or liquid forms. Examples of solid forms are dusts, granules, tablets, powders and the like. Examples of liquid forms are emulsifiable concentrates, flowables and pastes. Such compositions may contain, in addition to the active compound or compounds,various carriers or diluents; surface active agents (wetting agents, dispersing agents and/or emulsifying agents); solvents (water, or organic solvents such as aromatic solvents or chlorinated aliphatic solvents); adhesives, tnhickeners, binders; antifoaming agents; and other substances as mentioned herein. Solid carriers or diluents included in such compositions or formulations may include, for example, ground natural minerals such as kaolins, alumina, calcium carbonate, silica, kieselguhr, clay, etc.; ground synthetic materials such as various silicates and aluminosilicates and ground vegetable products such as bark, cornmeal, sawdust, cellulose powder and the like.

To manufacture solid compositions, the active substances are mixed with solid carriers or diluents such as those mentioned above and the mixture is ground to the appropriate size. Granules can be manufactured by dissolving an active compound in an organic solvent and applying the mixture, for example, by atomization, onto an absorptive granulated inert material, such as silica. Adhesives may be utilized to assist in the incorporation of the compound onto the solid particles. Pellets or granules can be manufactured by extrusion with appropriate carriers and binders.

Wettable powders, flowables, and pastes are obtained by mixing and grindingan active compound with one or more dispersing agents and/or solid carriersor diluents. Also included may be wetting agents and/or dispersing agents, for example, lignins, methyl cellulose, naphthalenesulfonic acid derivatives, fatty alcohol sulfates and various types of alkali and alkaline earth metal salts of fatty acids.

Emulsifiable concentrates are generally obtained by dissolving the active compound in an organic solvent, for example, butanol, cyclohexanone, xylenes, or higher boiling aromatic hydrocarbons. To obtain suspensions oremulsions in water, wetting agents are generally also added.

It is possible to use highly concentrated liquid compositions containing upto about 95% by weight of the active compound, or even the active compound alone for those compounds which are liquids, when applying the compound inthe form of a finely divided liquid by use of various atomizing equipment, for example by airplane crop spraying techniques. For other purposes, however, the various types of compositions which can be utilized for thesecompounds will contain varying amounts of the compound according to the type of composition and the intended use.

In general, compositions may contain from 0.1 to 95% of the active compound, more preferably from 0.5 to 90%. Some typical compositions will contain an active compound as follows: wettable powders, flowables and pastes--20 to 90% active compound; oil suspensions, emulsions, solutions and emulsifiable concentrates--5 to 90% active compound; aqueous suspensions--10 to 50% active compound; dusts and powders--1 to 25% activecompound; granules and pellets--1 to 20% active compound.

The rate of application of the active compound to a locus to be controlled will depend on the activity of the compound and/or composition and the nature of the seeds and plants to be controlled and will vary from about 0.05 to about 50 pounds per acre (about 0.06 to about 56 kg/ha).

In addition to the active compound and the various agents utilized in preparing compositions and formulations mentioned above, such compositionsmay also contain one or more other active compounds of the type mentioned herein as well as other pesticidal agents, such as herbicides, fungicides,insecticides, acaricides, nematocides, bactericides, and plant growth regulators. Such compositions may also contain soil disinfectants or fumigants and may further contain fertilizers, thus making it possible to provide multi-purpose compositions containing one or more of the compoundsdescribed herein as well as, optionally, other pesticides and also fertilizers, all intended and formulated for use at the same locus.

Compositions containing one or more of the active compounds described, in aherbicidally effective amount, may be applied to the plant or locus to be controlled in any conventional manner. Thus, powders and various liquid compositions containing the active compound can be applied by the use of power dusters, boom and hand sprayers and spray dusters, or applied from airplanes as mists or sprays. When applied in the latter method they may be effective in very low dosages. To modify or control growth of germinating seeds or emerging seedlings liquid compositions may be appliedto the soil with conventional methods and may be distributed in the soil toa depth of one-half inch below the soil surface. The compositions need not be admixed with the soil particles but can be applied merely by sprinklingon the surface of the soil.

Compositions including active compounds may also be applied by addition to irrigation waters supplied to the field to be treated. This method of application permits penetration of the compounds into the soil as the water is absorbed therein.

EXAMPLES OF TYPICAL COMPOSITIONS

    ______________________________________                                         Oil                                                                            Ingredient           Weight %                                                  ______________________________________                                         Active Compound      1                                                         Oil solvent-heavy aromatic naphtha                                                                  99                                                        Total                100                                                       ______________________________________                                         Emulsifiable Concentrate                                                       Active Compound      50                                                        Kerosene             45                                                        Emulsifying agent (mixture of long                                             chain ethoxylated polyethers with                                              long chain sulfonate)                                                                               5                                                         Total                100                                                       ______________________________________                                         Emulsifiable Concentrate                                                       Active Compound      90                                                        Kerosene             5                                                         Emulsifying agent (mixture of long                                             chain ethoxylated polyethers with                                              long chain sulfonate)                                                                               5                                                         Total                100                                                       ______________________________________                                         Dusts and/or Powders                                                           Ingredient        Wt. %    Wt. %    Wt. %                                      ______________________________________                                         Active Compound   0.5      50.0     90.0                                       Attapulgite Clay Powder                                                                          93.5     44.0     4.0                                        Sodium lignin sulfonate                                                                          5.0      5.0      5.0                                        Sodium dioctyl sulfosuccinate                                                                    1.0      1.0      1.0                                        Total             100.0    100.0    100.0                                      ______________________________________                                     

What is claimed is:
 1. A compound having the formula ##STR20## in which W is oxygen or sulfur;X is hydrogen, halogen, nitro, cyano, perhalomethyl, difluoromethyl, pentafluoroethyl, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, trifluoromethylthio, difluoromethoxy, trifluoromethoxy, tetrafluoroethoxy, methylsulfonyl, trifluoromethylsulfonyl, phenoxy, pyridyloxy, halo-substituted-phenoxy or -pyridyloxy, trifluoromethyl-substituted-phenoxy or -pyridyloxy, C₁ -C₄ alkyloximinomethyl, benzyloximinomethyl, 1-(C₁ -C₄ alkyl)oximinoethyl and 1-benzyloximinoethyl; Y is hydrogen, halogen, nitro, cyano, perhalomethyl, difluoromethyl, pentafluoroethyl, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, trifluoromethylthio, trifluoromethoxy, tetrafluoroethoxy, methylsulfonyl and trifluoromethylsulfonyl; Z is hydrogen or fluoro if Y is hydrogen, or hydrogen if Y is other than hydrogen; R₁ is hydrogen, methyl, ethyl or chloromethyl; A is oxygen, sulfur, ##STR21## in which R₃ and R₄ are independently hydrogen, methyl or methoxy; and R₂ is C₁ -C₆ alkyl; carbo(C₁ -C₆)-alkoxy; carbo(C₁ -C₆)alkoxy(C₁ -C₂ alkylene); C₁ -C₄ haloalkyl if m is 1; C₂ -C₄ haloalkyl if m is 0; C₁ -C₅ alkoxy; C₃ -C₆ cycloalkyl optionally substituted by up to 2 methyl groups; C₂ -C₆ alkenyl; phenyl; substituted phenyl in which the substituents are C₁ -C₄ alkyl, halogen, trifluoromethyl, nitro, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, or cyano; phenoxy; halosubstituted phenoxy; styryl; p-chlorophenylsulfonyl; C₂ -C₄ haloalkylcarbonyl; naphthyl; benzoyl; halosubstituted benzoyl; a polycyclic aliphatic group having from 6 to 12 carbon atoms; amino; mono- or di-(C₁ -C₄)alkylamino; C₃ -C₈ alkynyl; cyano; benzyl; or a saturated or unsaturated heterocyclic ring containing from 5 to 6 atoms including from 1 to 2 hetero atoms selected from oxygen and sulfur, optionally substituted by from 1 to 3 methyl groups and/or from 1 to 2 oxo groups; and m is 0 or 1;provided that: (a) when A is --NH-- and R₂ is phenyl or substituted phenyl, then W is oxygen; and (b) when A is oxygen and R₂ is substituted phenyl, the substituents on the phenyl ring are not meta-directing electron-withdrawing groups; and (c) when R₂ is cyano or C₃ -C₈ alkynyl and m is 1, then A is --CH₂ --.
 2. A compound according to claim 1 in which Y and Z are hydrogen.
 3. A compound according to claim 1 in which X is halo, nitro, perhalomethyl, di- or trifluoromethoxy, difluoromethyl or tetrafluoroethoxy.
 4. A compound according to claim 3 in which Y and Z are hydrogen.
 5. A compound according to claim 1 in which Y is hydrogen and Z is fluoro.
 6. A compound according to claim 1 in which Y is 5-halo or 5-trifluoromethyl.
 7. A compound according to claim 1 in which m is
 0. 8. A compound according to claim 7 in which R₂ is C₁ -C₆ alkyl, C₂ -C₆ alkenyl, C₂ -C₄ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₆ carboalkoxy, C₁ -C₆ carboalkoxy-(C₁ -C₂)-alkylene, di-C₁ -C₄ alkylamino or a 5- to 6-membered saturated or unsaturated heterocyclic ring containing from 1 to 2 oxygen or sulfur atoms.
 9. A compound according to claim 1 in which m is 1 and Z is oxygen, sulfur, CH₂ or --NH--.
 10. A compound according to claim 9 in which R₂ is C₁ -C₆ alkyl, C₁ -C₅ alkoxy, C₁ -C₆ carboalkoxy; C₁ -C₆ carboalkoxy-(C₁ -C₂)-alkylene, C₃ -C₆ cycloalkyl, halophenoxy, p-chlorosulfonyl, C₂ -C₆ alkenyl, C₂ -C₄ haloalkylcarbonyl, halosubstituted phenyl or a 5- or 6-membered saturated or unsaturated heterocyclic ring containing 1 or 2 sulfur or oxygen atoms.
 11. A compound according to claim 1 in which W is oxygen; X is trifluoromethyl or halo; Y is hydrogen; Z is hydrogen and R₁ is ethyl.
 12. A compound according to claim 11 in which R₂ is C₁ -C₆ alkyl, C₂ -C₆ alkenyl, C₁ -C₅ alkoxy, C₁ -C₄ haloalkyl, if m is 1; C₂ -C₄ haloalkyl is m is 0; C₃ -C₆ cycloalkyl, di-(C₁ -C₄ alkyl)amino, halosubstituted phenyl, halo-substituted phenoxy, p-chlorophenylsulfonyl, C₂ -C₄ haloalkylcarbonyl, C₁ -C₆ carboalkoxy, C₁ -C₆ carboalkoxy-(C₁ -C₂)alkylene or a 5- to 6-membered saturated or unsaturated heterocyclic ring containing 1 or 2 oxygen or sulfur atoms.
 13. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is hydrogen, W is oxygen, m is 0; R₁ is ethyl and R₂ is isobutyl.
 14. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is hydrogen, W is oxygen, m is 1, A is oxygen; R₁ is ethyl and R₂ is isopropyl.
 15. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is hydrogen, W is oxygen, m is 0; R₁ is ethyl and R₂ is cyclopropyl.
 16. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is hydrogen, W is oxygen, m is 1, A is oxygen; R₁ is ethyl and R₂ is 3-tetrahydrofuryl.
 17. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is hydrogen, W is oxygen, m is 0; R₁ is ethyl and R₂ is secondary butyl.
 18. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is hydrogen, W is oxygen, m is 0; R₁ is ethyl and R₂ is neopentyl.
 19. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is hydrogen, W is oxygen, m is 0; R₁ is ethyl and R₂ is 3,3,3-trifluoro-2-methylpropyl.
 20. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is hydrogen, W is oxygen, m is 1, A is --CH₂ --; R₁ is ethyl and R₂ is cyclopentyl.
 21. A compound according to claim 1 in which X is chloro, Y is hydrogen, Z is fluoro, W is oxygen, m is 1, A is oxygen; R₁ is ethyl and R₂ is isopropyl.
 22. A compound according to claim 1 in which X is cyano, Y is hydrogen, Z is hydrogen, W is oxygen, m is 1, A is oxygen; R₁ is ethyl and R₂ is isopropyl.
 23. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is fluoro, W is oxygen, m is 1, A is oxygen; R₁ is ethyl and R₂ is isopropyl.
 24. A compound according to claim 1 in which X is chloro, Y is hydrogen, Z is hydrogen, W is oxygen, m is 1, A is oxygen; R₁ is ethyl and R₂ is isopropyl.
 25. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is hydrogen, W is oxygen, m is 1, A is --NH--; R₁ is ethyl and R₂ is ethyl.
 26. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is hydrogen, W is oxygen, m is 1, A is --NH--; R₁ is ethyl and R₂ is tertiary butyl.
 27. A compound according to claim 1 in which X is nitro, Y is hydrogen, Z is hydrogen, W is oxygen, m is 1, A is 0; R₁ is ethyl and R₂ is isopropyl.
 28. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is hydrogen, W is oxygen, m is 1, A is --CH₂ --; R₁ is ethyl and R₂ is 4-fluorophenyl.
 29. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is hydrogen, W is oxygen, m is 0; R₁ is ethyl and R₂ is 1-methylcyclopropyl.
 30. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is hydrogen, W is oxygen, m is 0; R₁ is ethyl and R₂ is trans-2-methylcyclopropyl.
 31. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is hydrogen, W is oxygen, m is 1, A is oxygen; R₁ is chloromethyl and R₂ is isopropyl.
 32. A compound according to claim 1 in which X is trifluoromethyl, Y is hydrogen, Z is fluoro, W is oxygen, m is 0; R₁ is ethyl and R₂ is cyclopropyl.
 33. An herbicidal composition containing (a) a herbicidally effective amount of a compound according to claim 1 and (b) a herbicidally suitable inert diluent or carrier.
 34. A method of controlling undesirable vegetation comprising applying to said vegetation or the locus thereof a herbicidally effective amount of a compound according to claim
 1. 35. A method of controlling undesirable vegetation comprising applying to said vegetation or the locus thereof a herbicidally effective amount of a composition according to claim
 33. 